3-(2,5-Dimethyl-phenylsulfanyl)-propionic acid → 5,8-Dimethyl-3,4-dihydro-2H-1-benzothiopyran-4-one

HRID 378808Notes

Reaction equation

HRID 378808 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9][CH2:10][CH2:11][C:12]([OH:14])=O>S(=O)(=O)(O)O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]2[C:4]=1[C:12](=[O:14])[CH2:11][CH2:10][S:9]2

Participants

3

Reactant 1

HCID 167883143-(2,5-Dimethyl-phenylsulfanyl)-propionic acid

Product 1

HCID 216965945,8-Dimethyl-3,4-dihydro-2H-1-benzothiopyran-4-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

At −10° C., 100 g (0.48 mol) of 3-[(2,5-dimethylphenyl)thio]propanoic acid were dissolved in 2200 ml of conc. sulfuric acid. The reaction solution was stirred at room temperature for 1 h and then poured onto crushed ice. The aqueous solution was extracted with a diethyl ether/hexane mixture (1:9) (6×500 ml). The combined organic phases were dried over MgSO4 and concentrated completely using a rotary evaporator.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionThe aqueous solution was extracted with a diethyl ether/hexane mixture (1:9) (6×500 ml)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated completely
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-deb8b6b04f2a40bdafff15b2284c9305
Source dataset
uspto-grants-2001_10
Patent number
US06297196B1

Reaction notes

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